2-(((tert-butyldimethylsilyl)oxy)methyl)-1H-benzo[d]imidazole | 307931-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(((tert-butyldimethylsilyl)oxy)methyl)-1H-benzo[d]imidazole
• 英文别名: 2-Tert-butyldimethylsilyloxymethylbenzimidazole；1H-benzimidazol-2-ylmethoxy-tert-butyl-dimethylsilane
• CAS: 307931-38-0
• 化学式: C₁₄H₂₂N₂OSi
• 分子量: 262.427
• InChiKey: MCSDUXSCNZIMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(((tert-butyldimethylsilyl)oxy)methyl)-1H-benzo[d]imidazole 在 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Analogues of the Pan Class I Phosphatidylinositol 3-Kinase (PI3K) Inhibitor 2-(Difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474)

  摘要：

  A structure activity relationship (SAR) study of the pan class I PI 3-kinase inhibitor 2-(difluoromethyl)-1-[4,6-di(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole (ZSTK474) identified substitution at the 4 and 6 positions of the benzimidazole ring as having significant effects on the potency of substituted derivatives. The 6-amino-4-methoxy analogue displayed a greater than 1000-fold potency enhancement over the corresponding 6-aza-4-methoxy analogue against all three class Ia PI 3-kinase enzymes (p110 alpha, p110 beta, and p110 delta) and also displayed significant potency against two mutant forms of the p110 alpha isoform (H1047R and E545K). This compound was also evaluated in vivo against a U87MG human glioblastoma tumor xenograft model in Ragl(-/-) mice, and at a dose of 50 mg/kg given by ip injection at a qd x 10 dosing schedule it dramatically reduced cancer growth by 81% compared to untreated controls.

  DOI：

  10.1021/jm200688y
• 作为产物：
  描述：

  2-羟甲基苯并咪唑 、 叔丁基二甲基氯硅烷 在 吡啶 作用下， 反应 4.0h， 以100%的产率得到2-(((tert-butyldimethylsilyl)oxy)methyl)-1H-benzo[d]imidazole
  参考文献：
  名称：

  含有稠环丙烷环的吡咯并吡啶并[1,2-a]苯并咪唑醌抗肿瘤剂的合成

  摘要：

  通过 N-(烯丙基和丁-3-烯基)苯并咪唑-2-Eschenmoser 热解产生的重氮亚甲基环加成，环丙烷环已稠合到四氢吡咯并-和四氢吡啶并-[1,2-a]-苯并咪唑和苯并咪唑醌上腙（氮丙啶亚胺）。在较低温度下，仅 N-烯丙基苯并咪唑-2-Eschenmoser 腙得到 1,3-偶极 [3 + 2] 环加合物。

  DOI：

  10.1055/s-2005-861832

文献信息

• [EN] COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DU FACTEUR INHIBITEUR DE LA MIGRATION DES MACROPHAGES
  申请人：IMMUNOPHAGE BIOMEDICAL CO LTD

  公开号：WO2020186220A1

  公开（公告）日：2020-09-17

  The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.

  本发明提供了上述公式(I)所示的化合物及其药用可接受的盐、溶剂化物、异构体或前药，以及含有这些化合物的药物组合物。本发明还提供了一种用于治疗由巨噬细胞迁移抑制因子介导的疾病的方法，包括向需要治疗的对象施用本发明的化合物或药物组合物。
• NOVEL HETEROCYCLIC COMPOUND
  申请人：DAEWOONG PHARMACEUTICAL CO., LTD.

  公开号：US20170088551A1

  公开（公告）日：2017-03-30

  The present invention relates to a compound represented by chemical formula 1, which can be used for the prevention and treatment of diseases caused by abnormality in a prolyl-tRNA synthetase (PRS) activity, or a pharmaceutically acceptable salt thereof, a method for preparing the same, and a pharmaceutical composition comprising the same.

  本发明涉及一种化学式1所代表的化合物，可用于预防和治疗由脯氨酰-tRNA合成酶（PRS）活性异常引起的疾病，或其药用盐，以及制备该化合物的方法和包含该化合物的药物组合物。
• Substituted phenylcyclohexane carboxylic acid amides that have an adenosine uptake inhibiting effect
  申请人：Bayer Healthcare AG

  公开号：US20040186106A1

  公开（公告）日：2004-09-23

  The present invention relates to substituted phenylcyclohexanecarboxamides of the formula (I) having adenosine-uptake-inhibiting action, to a process for their preparation and to their use in medicaments, in particular for treating ischaemic brain disorders. 1

  本发明涉及公式（I）的取代苯基环己烷羧酰胺，具有腺苷摄取抑制作用，以及它们的制备过程和在药物中的使用，特别是用于治疗缺血性脑疾病。
• Substituted phenylcyclohexane carboxylic acid amides and their use as adenosine uptake inhibitors
  申请人：Bayer Aktiengesellschaft

  公开号：US06984642B1

  公开（公告）日：2006-01-10

  The present invention relates to substituted phenylcyclohexanecaboxamides of the formula (I), to processes for their preparation and to their use in medicaments, in particular for treating cardiovascular disorders.

  本发明涉及式(I)的取代苯基环己烷羧酰胺，其制备方法和它们在药物中的应用，特别是用于治疗心血管疾病。
• QUINAZOLINES AND AZAQUINAZOLINES AS DUAL INHIBITORS OF RAS/RAF/MEK/ERK AND PI3K/AKT/PTEN/MTOR PATHWAYS
  申请人：ASANA BIOSCIENCES, LLC

  公开号：US20160068496A1

  公开（公告）日：2016-03-10

  The present application provides novel quinazolines and azaquinazolines and pharmaceutically acceptable salts thereof. Also provided are methods for preparing these compounds. These compounds are useful in for co-regulating RAS/RAF/MEK/ERK and PI3K/AKT/PTEN/mTOR pathways by administering a therapeutically effective amount of one or more of the compounds of formula (I), wherein X, Y, T and R 4 , and R 6 to R 8′ are defined herein, to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the RAS/RAF/MEK/ERK and PI3K/AKT/PTEN/mTOR pathways. A variety of conditions can be treated using these compounds and include diseases which are characterized by abnormal cellular proliferation. In one embodiment/the disease is cancer.

  本申请提供了新型的喹唑啉和氮杂喹唑啉及其药学上可接受的盐。还提供了制备这些化合物的方法。通过向患者投予公式（I）中的一个或多个化合物的治疗有效量，其中X、Y、T和R4以及R6到R8'在此定义，这些化合物在共同调节RAS / RAF / MEK / ERK和PI3K / AKT / PTEN / mTOR途径方面是有用的。通过这样做，这些化合物对治疗与RAS / RAF / MEK / ERK和PI3K / AKT / PTEN / mTOR途径失调有关的疾病具有有效性。这些化合物可用于治疗多种疾病，包括以异常细胞增殖为特征的疾病。在一个实施例中，该疾病是癌症。